Description

Dibromo[(S)-(-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II) (CAS: 366488-99-5) is a highly specialized chiral palladium complex designed for asymmetric catalysis and advanced synthetic applications. With the molecular formula C₄₄H₃₄Br₂P₂Pd⁺², this compound features a binaphthyl backbone coordinated to palladium(II) with diphenylphosphino ligands, ensuring exceptional enantioselectivity in cross-coupling reactions. Ideal for researchers and scientists in organic chemistry, pharmaceuticals, and materials science, this air- and moisture-sensitive reagent is supplied with rigorous purity standards (typically ≥95% by HPLC) and must be stored under inert conditions. Its precise steric and electronic tuning makes it indispensable for Suzuki-Miyaura, Heck, and Negishi couplings, as well as other C-C bond-forming transformations requiring high enantiomeric excess (ee).

Properties

• CAS Number: 366488-99-5
• Complexity: 800
• IUPAC Name: dibromopalladium;[1-(2-diphenylphosphaniumyl-1-naphthyl)-2-naphthyl]-diphenyl-phosphonium
• InChI: InChI=1S/C44H32P2.2BrH.Pd/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38;;;/h1-32H;2*1H;/q;;;+2
• InChI Key: XOOQZGNLBGHEEX-UHFFFAOYSA-N
• Exact Mass: 889.95168
• Molecular Formula: C44H34Br2P2Pd+2
• Molecular Weight: 890.9
• SMILES: C1=CC=C(C=C1)[PH+](C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)[PH+](C7=CC=CC=C7)C8=CC=CC=C8.Br[Pd]Br
• Monoisotopic Mass: 887.95373
• Synonyms: 366488-99-5, Dibromo[(S)-(-)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II)

This chiral palladium complex is widely used in asymmetric synthesis, particularly for enantioselective cross-coupling reactions to construct stereogenic centers in pharmaceuticals and agrochemicals. It excels in Suzuki-Miyaura couplings of aryl halides with boronic acids, delivering high ee values in chiral biaryl synthesis. Researchers also employ it in Heck reactions for stereocontrolled alkene functionalization. Its stability under mild conditions makes it suitable for lab-scale and industrial applications.

Safety and Hazards

GHS Hazard Statements

• H302+H312+H332 (100%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (100%)
• STOT SE 3 (100%)

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